28+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Vermont
  3. Central Vermont- Killington
  4. Chittenden

Chittenden pickleball Stays, Resort Rentals, & Homes

About Chittenden Vacation Rentals

Discover over 28 amazing vacation rental options in Chittenden with pickleball courts or nearby facilities. From resorts to hotels, villas to condos, PickleTrip connects you with a vast selection of pickleball-ready amenities at great prices, providing you with the perfect spot to base your next pickleball vacation. Stay and Play pickleball When You Travel and uncover great stays in Chittenden.

Find exclusive last-minute deals on vacation rentals, resorts, and hotels with private courts and nearby facilities with PickleTrip™, whether you're traveling solo or with a group. Our platform offers a variety of stay options, from vacation rentals to Airbnb-style properties, all with private pickleball courts or nearby facilities. Compare options from multiple suppliers with a single click to find the perfect stay that fits your budget and style. Places to stay near pickleball courts are an average of 878.45 ft², with prices averaging US $615 per night.

With PickleTrip™, you can easily search for and book your next pickleball vacation rental with courts or nearby facilities. Our platform connects you with the ideal holiday rental to create a lifetime of travel memories. Prices listed are often discounted versus rack rates, so you can secure your perfect place to stay today and get ready to play pickleball in Chittenden.

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Top Pickleball-Ready Accommodation Types in Chittenden

Type Count
Vacation Homes 21
Holiday Apartments 3

Use these Quick Filters to Find a Vacation Rental in Chittenden

★ Pro Tip: PickleTrip™ is a travel platform, connecting avid pickleball players and enthusiasts with a variety of vacation rentals, resorts, and hotels featuring private pickleball courts or nearby facilities. We curate a vast selection of properties from trusted sources, providing you with unbeatable options and pricing to find the perfect pickleball getaway. Experience unforgettable pickleball matches in Chittenden with PickleTrip™.

Weather in Chittenden, VT

View the weather forecast for Chittenden before booking your Chittenden Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Chittenden, VT

PickleTrip offers a large selection of top attractions around Chittenden . Research things to do on your vacation before you visit Chittenden.


Lefferts Pond
Killington Resort
Killington Peak
Pico Mountain at Killington Ski Resort
Green Mountain National Forest
Castleton University
Lake Bomoseen
Pico Peak
Little Pico Mountain
Paramount Theater
Rutland Regional Medical Center
Lake Saint Catherine
Lake Dunmore
Rutland Country Club
Suicide Six Ski Area
Killington Golf Course
Woodstock Country Club
Billings Farm and Museum
Middlebury College Snow Bowl Ski Area
Branbury State Park

Other Places to Stay in Chittenden, VT


Lefferts Pond 24 Properties

Frequently Asked Questions About Chittenden?

What are the top vacation rentals, resorts, and hotels in Chittenden with Courts?

Experience the ultimate pickleball vacation with PickleTrip™. We offer a variety of premium rental properties, resorts, and hotels with private pickleball courts or nearby facilities in Chittenden. Whether you're a beginner or a seasoned player, we have the perfect destination for you to stay and play. Book now and discover the best pickleball vacation spots in Chittenden!

Which vacation rentals, resorts, or hotels in Chittenden is best for families looking for a pickleball-getaway?

Looking for a fun and active getaway with pickleball courts in Chittenden? With PickleTrip™, you'll have access to a wide selection of top-rated properties that offer private pickleball courts or nearby facilities. Make the most of you getaway and ace your A-game while you travel.

How many PickleTrip vacation rentals or resorts are available in Chittenden?

PickleTrip™ offers a diverse selection of properties with private pickleball courts or nearby facilities to enhance your pickleball experience on your next trip. With a combination of established great stays and new options in top locations, PickleTrip™ has over 28 properties listed in Chittenden in 2026, and the number only continues to grow. By consolidating listings from various providers, PickleTrip™ brings you the best luxury stays for a sporty, professional, and fun travel experience.


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There are 28 Chittenden, VT Vacation Rentals

Recently Booked Vacation Rentals in Chittenden